Now that I've shared the new Fresh Look / Revisited review of the Carpenters album Made in America (Parts One and Two- coming next month), I thought I'd have a little fun with AI and ask a few engines to create something interesting.
Die hard fans of Karen Carpenter's smoothly golden contralto readily acknowledge she was born to sing the classics of the Great American Songbook. Her brother Richard repeatedly told interviewers he knew she was perfect for this time period. The Carpenters recorded only four from this era: When I Fall in Love, Little Girl Blue, I Can Dream, Can't I? and From This Moment On. All this not including her duet with Ella Fitzgerald on Music, Music, Music. Unfortunately, Karen's untimely death in 1983 ended any future plans to record others.
Thanks to AI, it's easy to put together studio concepts and songlists. So I thought it would be a fun little exercise to do just that, imagining what a Great American Songbook album might look like for her. Then, I decided it would be even more fun to compare them. For this experiment I chose ChatGPT, Microsoft CoPilot, and Google Gemini.
I used the same prompt with all three: "Craft an imaginary song list from the Great American Songbook tailor made for singer Karen Carpenter if she had lived. Take into account her warm contralto and storytelling capabilities with her ability to sound personal and vulnerable. 12 songs long." Imperfect and incomplete, but hey, I was a bit under the weather when I conceived the idea.
My Questions-
1- Would these AI platforms even know Karen and Richard recorded these four songs?
2- Would similar songs choices appear on their proposed song lists?
3- Does Richard have a role to play on this project?
4- What would the platforms' visual representation of the proposed album look like?
5- If the program had to pick one song as a best representation of Karen singing this era's tunes, which one would it be and why?
Each platform goes from these questions to different possibilities, including imaginary liner notes from Richard to creating arrangements or each song chosen and why. Some even offer to create an album cover. The mind reels with possibilities.
Ready to see the results? Let's go!
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ChatGPT:
"Absolutely! I’ve crafted a 12-song imaginary Great American Songbook set specifically for Karen Carpenter, focusing on her warm, intimate contralto, her natural phrasing, and her gift for making every song feel personal and vulnerable. This list balances ballads, tender storytelling songs, and a few mid-tempo numbers to showcase nuance."
“Karen Sings the Songbook” – Imaginary Setlist
“Someone to Watch Over Me” (Gershwin)
Tender, heartfelt; Karen’s contralto would make this a quiet, intimate confessional.“The Very Thought of You” (Ray Noble)
Soft, lush phrasing perfect for her warm tonal color; the song becomes almost a whisper of devotion.“It Had to Be You” (Isham Jones / Gus Kahn)
A storytelling piece where she could convey both vulnerability and wry charm.“You Don’t Know What Love Is” (Gene de Paul / Don Raye)
Dark, melancholic ballad; her emotional transparency would make the heartbreak palpable.“But Not for Me” (Gershwin)
A slightly ironic, wistful tune, allowing her to tell a story with gentle phrasing.“I’ve Got a Crush on You” (Gershwin)
Sweet, vulnerable longing; ideal for her understated romantic style.“The Nearness of You” (Hoagy Carmichael / Ned Washington)
Classic intimacy; Karen could make this sound like a private confession.“Skylark” (Hoagy Carmichael / Johnny Mercer)
Expansive, poetic; a song that allows her to float emotionally while maintaining her signature warmth.“Bewitched, Bothered and Bewildered” (Rodgers & Hart)
Ideal for her storytelling ability; she could make the self-doubt feel tender rather than bitter.“My Funny Valentine” (Rodgers & Hart)
A timeless ballad where her subtle vibrato would bring out every nuance of vulnerability.“You Made Me Love You” (James V. Monaco / Joseph McCarthy)
A playful, innocent love song, perfectly suited to her ability to be heartfelt without over-singing.“As Time Goes By” (Herman Hupfeld)
A warm, nostalgic closer, where she could wrap the listener in timeless intimacy.Let’s imagine this as a full Karen Carpenter Great American Songbook album, thoughtfully sequenced for emotional impact, pacing, and her warm contralto storytelling. I’ll include tempo, mood, and arrangement ideas to bring it to life:
Album Concept: “Karen Sings the Songbook”
1. “Someone to Watch Over Me” – Ballad, intimate
Soft piano, subtle strings. Opens the album with tender vulnerability, Karen almost whispering the lyrics as if confiding in the listener.
2. “I’ve Got a Crush on You” – Slow swing, romantic
Light brushed drums, gentle horns. A warm, fluttering, hopeful love song that shows innocence without sentimentality.
3. “The Very Thought of You” – Ballad, lush
Full string arrangement, minimalist piano. Her phrasing lets each word linger, emphasizing longing and devotion.
4. “It Had to Be You” – Mid-tempo, storytelling
Upright bass, soft brushes, subtle guitar. She tells the story with wry charm, playing with small inflections for emotional color.
5. “You Don’t Know What Love Is” – Slow, melancholic
Sparse arrangement: piano, soft cello. She delivers heartbreak with understated emotional transparency, pulling the listener close.
6. “But Not for Me” – Light swing, wistful
Gentle horns and brushed drums. A touch of irony in her voice, bittersweet without ever sounding detached.
7. “The Nearness of You” – Tender ballad
Lush strings, soft piano. A private, intimate performance; her voice hovers over each note like a caress.
8. “Skylark” – Expansive ballad
Rich orchestration, airy harp, soft strings. Emotional and poetic, she can sustain long notes without strain, evoking wistful yearning.
9. “Bewitched, Bothered and Bewildered” – Medium-slow, expressive
Swinging but restrained rhythm section. Her storytelling shines; every inflection communicates self-doubt and charm.
10. “My Funny Valentine” – Slow, introspective
Minimalist jazz trio: piano, bass, brushes. Karen’s voice conveys both tenderness and a quiet, self-aware melancholy.
11. “You Made Me Love You” – Uplifting, playful
Light swing, strings and soft brass. Brightens the mood before the closer, playful innocence in phrasing and vibrato.
12. “As Time Goes By” – Nostalgic, warm closer
Gentle full orchestra, soft brush drums. Ends the album with timeless intimacy, her voice wrapping the listener in comfort and reflection.
This flow:
Starts with intimate vulnerability,
Moves through hopeful romance, bittersweet reflection, and playful charm,
Peaks with emotional storytelling,
Then closes in nostalgic warmth, leaving the listener feeling personally touched.
If you want, I can also create a visual “album concept cover” that matches this imagined Karen Carpenter vibe—soft light, warm tones, maybe her with a vintage microphone. It could feel like an actual lost album cover.
"If I had to choose one song from the twelve that most perfectly fits Karen Carpenter’s voice and style, it would be:
“The Nearness of You”
Why this one above all the others:
Warm, intimate phrasing: Karen excelled at making a song feel like a private conversation. This song practically requires that kind of emotional intimacy.
Contralto richness: Its long, gentle melodic lines sit right in the sweet spot of her lower-to-middle register, where her voice was at its most velvety and effortless.
Emotional honesty: Karen had a rare ability to sound vulnerable without seeming fragile. “The Nearness of You” is all about quiet emotional truth—the kind she delivered better than almost anyone.
Unforced storytelling: The song’s simplicity is its strength, and Karen was a master at elevating simple lyrics through tone, breath, and sincerity.
In an imagined recording, her voice would sit close to the microphone, warm and breathy, with a minimal arrangement—piano, soft strings—making the song feel like a whispered confession."
My Evaluation- Great song selection with a couple of unexpected choices, You Don't Know What Love Is and You Made Me Love You. Great variety of styles and tempo. So many of these were recorded by Linda Ronstadt beginning in 1983, it is easy to imagine Karen doing the same. No mention of Richard playing a role. No mention of previously recorded songs from the era. The generated image is totally generic, uninspired and fully unimaginative.
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Copilot:
"Here’s a carefully imagined 12‑song setlist from the Great American Songbook tailored for Karen Carpenter’s warm contralto, her gift for intimacy, and her ability to make every lyric feel like a personal confession. I’ve chosen songs that lean into vulnerability, storytelling, and emotional resonance—qualities she excelled at."
Karen Carpenter’s Imagined Great American Songbook Album
“Someone to Watch Over Me” (George & Ira Gershwin)
Perfect for her tender, almost whispered delivery—she could make it feel like a prayer.
“The Nearness of You” (Hoagy Carmichael / Ned Washington)
Her contralto would wrap around the melody with understated longing.
“But Not for Me” (George & Ira Gershwin)
A bittersweet lyric that suits her ability to sound resigned yet hopeful.
“My Foolish Heart” (Victor Young / Ned Washington)
Vulnerability at its core—Karen could make this heartbreak sound achingly sincere.
“I Get Along Without You Very Well” (Hoagy Carmichael)
Understated melancholy, tailor‑made for her storytelling style.
“Skylark” (Hoagy Carmichael / Johnny Mercer)
Her voice would give this dreamy ballad a grounded, human ache.
“Here’s That Rainy Day” (Jimmy Van Heusen / Johnny Burke)
She could turn this into a hushed, rainy‑window moment of reflection.
“In the Wee Small Hours of the Morning” (David Mann / Bob Hilliard)
A late‑night confessional, perfectly suited to her intimate phrasing.
“Blame It on My Youth” (Oscar Levant / Edward Heyman)
She’d bring a fragile honesty to this lyric about regret and innocence.
“I’ll Be Seeing You” (Sammy Fain / Irving Kahal)
Nostalgic and deeply personal—her voice would make it feel like a letter home.
“When Sunny Gets Blue” (Marvin Fisher / Jack Segal)
A song of quiet sorrow, ideal for her ability to convey empathy.
“Ev’ry Time We Say Goodbye” (Cole Porter)
A closing track full of poignancy, her voice lingering like a farewell embrace.
Why these songs? Karen Carpenter’s artistry was about restraint, intimacy, and emotional truth. Unlike belters, she didn’t overpower—she invited listeners in. This setlist emphasizes melancholy, longing, and quiet storytelling, giving her space to make each lyric feel lived‑in and personal.
Here’s a fully imagined studio album concept for Karen Carpenter’s Great American Songbook project, designed as if she had lived to record it. I’ve sequenced the songs for flow, suggested arrangements, and envisioned a cover photo that captures her timeless warmth and vulnerability."
Album Concept: In the Wee Small Hours
(An Imagined Karen Carpenter Songbook)
Tracklist & Flow
“Someone to Watch Over Me” – Opens with hushed strings and piano, setting a prayerful tone.
“The Nearness of You” – Gentle brush‑drums and upright bass, intimate and close‑mic’d.
“But Not for Me” – Light swing with subtle jazz guitar, her voice carrying bittersweet humor.
“My Foolish Heart” – Orchestral ballad, lush but restrained, spotlighting her contralto.
“I Get Along Without You Very Well” – Sparse piano, almost confessional.
“Skylark” – Dreamy woodwinds and harp, evoking longing.
“Here’s That Rainy Day” – Mid‑album reflective moment, brushed cymbals and muted trumpet.
“In the Wee Small Hours of the Morning” – Title track, late‑night intimacy, minimal arrangement.
“Blame It on My Youth” – Fragile honesty, strings swelling only at the end.
“I’ll Be Seeing You” – Nostalgic, cinematic arrangement, evoking memory.
“When Sunny Gets Blue” – Gentle ballad with guitar and flute, empathetic tone.
“Ev’ry Time We Say Goodbye” – Closing farewell, orchestral swell fading into silence.
Arrangements & Production Notes
Producer Concept: Richard Carpenter (her brother) would likely oversee, ensuring authenticity and restraint.
Instrumentation: Piano, upright bass, brushed drums, strings, muted brass, occasional harp.
Vocal Treatment: Close‑mic’d, warm reverb, highlighting her storytelling intimacy.
Mood Arc: Begins with yearning, moves through bittersweet reflection, closes with poignant farewell.
Liner Notes (Excerpt)
“Karen’s voice was never about volume—it was about truth. These songs, chosen from the heart of the American Songbook, are not just standards. They’re stories. And Karen tells them with the grace of someone who’s lived every word.” —Richard Carpenter, Producer"
"If I had to choose just one song from the original twelve that best fits Karen Carpenter’s voice and style, it would be:
“In the Wee Small Hours of the Morning” (David Mann / Bob Hilliard)
Why it’s the perfect match:
Emotional intimacy: The lyric is quiet, reflective, and deeply personal—exactly the kind of emotional terrain Karen excelled in.
Vocal range: Its low, gentle phrasing sits perfectly in her warm contralto, allowing her to caress each word without strain.
Narrative tone: It’s a late-night confessional, full of longing and solitude. Karen had a way of making listeners feel like she was singing just to them, and this song invites that kind of closeness.
Production potential: With Richard’s signature arrangements—soft strings, brushed drums, and close-mic’d vocals—it could have become a definitive version.
My Evaluation- More good song choices with only two duplicates from the previous list. I did not know the song Here's That Rainy Day, and I loved the inclusion of Blame It On My Youth (Aaron Neville's version of this tune is stellar.) Again, there's no mention of previously recorded songs. Richard does get a role here. His imagined quote is something I could really hear him say. This generated image is unimaginative and not wistful or reflective. What is it with the boring brown tones?
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Google Genini:
"This is a wonderful concept. Karen Carpenter's voice, described as a "dark, melancholy alto" by some critics, would have been an absolute revelation in the world of the Great American Songbook. She had an uncanny ability to infuse even the most familiar melody with a devastatingly personal vulnerability.
Here is a 12-song tracklist for her imaginary album:
Karen Carpenter Sings The Great American Songbook
1. "I'm a Fool to Want You"
(Frank Sinatra/Jack Wolf/Jack Dorsey)
The Fit: A perfect opening statement. Its stark, wounded lyrics and melancholic melody would have been sung with a controlled, heart-breaking tremor. Her contralto could dive deep into the self-recrimination and despair of the lyric.
2. "Guess I'll Hang My Tears Out to Dry"
(Jule Styne/Sammy Cahn)
The Fit: A song about putting on a brave face after a great disappointment. Karen's signature blend of resilience and fragility—the "hanging out" of tears instead of crying them—is right in her wheelhouse.
3. "Skylark"
(Hoagy Carmichael/Johnny Mercer)
The Fit: A wistful, dreamy ballad about a singer waiting for her "skylark to come and to be a companion." Its gentle, soaring melody would showcase the warmth and purity of her upper-contralto register.
4. "The Man I Love"
(George & Ira Gershwin)
The Fit: A less vulnerable, but deeply personal track about an idealized, longed-for lover. Her interpretation would turn the standard into a quiet, hopeful soliloquy, anticipating the man who will "understand."
5. "Where Do You Start?"
(Johnny Mandel/Alan & Marilyn Bergman)
The Fit: While slightly later than the classic "Songbook" era, this is a masterclass in emotional complexity. It's about trying to quantify the precise moment a relationship began to fall apart. Karen's subtle delivery would capture the sheer exhaustion of a broken heart.
6. "I Get Along Without You Very Well (Except Sometimes)"
(Hoagy Carmichael/Jane Brown Thompson)
The Fit: A song of denial and quiet grief. The final, spoken parenthetical lyric—"except sometimes"—is tailor-made for her unique narrative gift, where a single, whispered phrase could convey worlds of loneliness.
7. "My Funny Valentine"
(Richard Rodgers/Lorenz Hart)
The Fit: The ultimate declaration of imperfect love. Karen's unadorned, sincere delivery would strip away any artifice, making the song feel like an intimate, living vow to a flawed, but deeply cherished, partner.
8. "I'm Glad There Is You (In a World of Trouble)"
(Jimmy Dorsey/Paul Madeira)
The Fit: A mid-album uplift. This track of gratitude and devotion would be a beautiful showcase for her rich, sustained notes, creating a moment of pure, adult romantic clarity.
9. "Spring Can Really Hang You Up the Most"
(Tommy Wolf/Fran Landesman)
The Fit: A devastating anti-Spring song. The sophisticated, self-deprecating lyric, "All alone by the telephone, nothing to say," feels like a cousin to her own work like "Rainy Days and Mondays." It demands a singer who can tell a story of modern alienation.
10. "Every Time We Say Goodbye"
(Cole Porter)
The Fit: This song about the bitter-sweet pain of departure, where each farewell teaches her a little more about whyshe loves, would be delivered with the gentle, aching precision that characterized her most moving work.
11. "Little Girl Blue"
(Richard Rodgers/Lorenz Hart)
The Fit: A song she actually recorded, and a perfect encapsulation of her appeal. It's an internal conversation, a tender plea to the self to "sing a sad refrain" and get through the night. It is the height of her vulnerable, personal storytelling.
12. "What'll I Do?"
(Irving Berlin)
The Fit: A simple, direct, and utterly forlorn closing note. Sung with just a piano and a subtle orchestral swell, Karen's voice would leave the listener with a feeling of deep, unresolved yearning.
Liner Notes: Karen Carpenter Sings The Great American Songbook
Produced and Arranged by Richard Carpenter
1. "I'm a Fool to Want You"
Instrumentation: Solo Piano (Richard Carpenter), Cello, and subtle Woodwinds.
The Vibe: Stark and intimate. The production is deliberately sparse, focusing all attention on Karen's voice, which is slightly dry (less reverb than usual) and close-miked. Richard's piano accompaniment provides simple, resonant chords in a low register, emphasizing the sense of isolation and regret.
2. "Guess I'll Hang My Tears Out to Dry"
Instrumentation: Jazz Quartet (Piano, Bass, Drums, muted Trumpet) and Strings (8-piece section).
The Vibe: A sophisticated, slow swing. The arrangement is elegant, with the strings swelling gently behind the vocal on key phrases. Karen's vocal delivery is measured and slightly defiant, with a beautifully controlled high note on the final phrase, suggesting the effort required to maintain composure.
3. "Skylark"
Instrumentation: Acoustic Guitar (playing the arpeggiated figure), French Horn, and lush Strings.
The Vibe: Pastoral and dreamy. This arrangement evokes a wide-open landscape. The French horn carries the secondary melodic line, creating a warm, golden timbre that perfectly complements Karen’s breathy, hopeful tone as she waits for her "skylark."
4. "The Man I Love"
Instrumentation: Full Orchestra, traditional sweeping Hollywood arrangement.
The Vibe: Grand and cinematic. This is the most traditional "Songbook" arrangement, with sweeping strings and a dramatic modulation before the final verse. Karen delivers the lyric with a quiet strength and conviction, making it sound less like a wish and more like a certainty.
5. "Where Do You Start?"
Instrumentation: Piano and a small Chamber Orchestra (Violas, Cellos, Flute).
The Vibe: Devastatingly reflective. The tempo is rubato (flexible), allowing Karen to take her time with the complex, conversational lyrics. The strings are mournful, and the bassline descends slowly on the bridge, mimicking the slow sinking feeling of realization. A truly vulnerable performance.
6. "I Get Along Without You Very Well (Except Sometimes)"
Instrumentation: Harp, Vibraphone, and Woodwind Choir (Clarinet, Oboe).
The Vibe: Ethereal and fragile. The arrangement emphasizes lightness and memory. The "Except Sometimes" is whispered and un-reverberated, an emotional breaking point captured with perfect clarity
7. "My Funny Valentine"
Instrumentation: Vocal, upright Bass, and light Brush Kit Drums.
The Vibe: Pure, unadorned reverence. The song is taken at an incredibly slow tempo, putting immense focus on Karen's sustained notes. There is no piano; the bass provides the harmonic foundation, giving the song a raw, late-night club feel. It’s an intimate portrait of acceptance.
8. "I'm Glad There Is You (In a World of Trouble)"
Instrumentation: Hammond Organ (used for harmonic sustain), electric Piano, and a gentle rhythm section.
The Vibe: Warm and steady. This arrangement has a slightly more contemporary early-70s feel—a subtle nod to Richard’s typical production—but used here to create a feeling of comfort and deep-seated gratitude. Karen's voice here is at its richest and most powerful.
9. "Spring Can Really Hang You Up the Most"
Instrumentation: Solo Acoustic Piano (fast and complex accompaniment) and Vocals.
The Vibe: Bitter and witty. The arrangement gives Richard a chance to showcase his jazzy, intricate piano style, mirroring the sophisticated melancholy of the lyric. Karen’s delivery is detached and observant, only breaking on the final, defeated line.
10. "Every Time We Say Goodbye"
Instrumentation: Strings, Oboe, and Tympani (very subtle).
The Vibe: Poetic and analytical. The Oboe carries a recurring, sad counter-melody. The arrangement builds slightly through the verses, reflecting the complexity of Cole Porter's structure, but retains an air of elegant sorrow.
11. "Little Girl Blue"
Instrumentation: Richard's iconic layered backing Vocals (a subtle, ghostly chorus), Piano, and Glockenspiel.
The Vibe: Self-soothing and heartbreaking. The inclusion of the multi-tracked Carpenters harmonies (always in the background, never overwhelming) serves as a familiar sonic touchstone, a comforting echo to the listener. Karen sings the lullaby to herself, making it the most personal track on the album.
12. "What'll I Do?"
Instrumentation: Solo Vocal, a single Acoustic Guitar (gentle fingerpicking), and a lingering String Drone.
The Vibe: The final breath. The song fades out on a sustained chord, leaving the question hanging. Karen’s vocal is soft and full of resignation, a perfect, quiet ending that captures the aching vulnerability that defined her artistry.
The Best Fit: "I Get Along Without You Very Well (Except Sometimes)"
(Hoagy Carmichael / Jane Brown Thompson)
Why It's The Perfect Match
The Power of Subtlety (The Whisper): Karen Carpenter's greatest strength was her ability to convey overwhelming sadness through understatement. The song builds to its parenthetical punchline: "(Except sometimes)." This line is not sung; it's a quiet, conversational confession that shatters the confident facade of the preceding verses. Karen's voice, which music critics often noted for its intimate, close-miked quality, would make that final whisper land with devastating emotional weight, making it feel like a secret shared with the listener alone.
The Contralto's Narrative Range: The song operates in a register that is low and melancholic, ideal for her warm contralto. She could use her "money in the basement" (her lower register) to establish the initial, resigned tone of self-sufficiency: "Of course, I get along fine." This deep, clear tone would ground the performance in mature, adult reflection.
Melancholy Meets Clarity: The melody is sophisticated but direct, allowing her renowned vocal clarity to shine. She doesn't need to employ vocal runs or belts; she just needs to tell the story. Her voice makes everything sound clean and pure, which provides a stark, painful contrast to the messy, unresolved grief the lyrics describe.
In short, this song is a masterclass in emotional complexity disguised as simple composure, and Karen Carpenter was the unmatched mistress of that very duality."
My Evaluation: OK, well at least the two previous AI lists and created content ended with an image that could only remotely pass for Karen. Not here. Not even close. Gemini is the only one of the three platforms to mention a song the Carpenters did record, Little Girl Blue. Richard gets producer and arranger credits here and even gets to plays the keyboards, a much deserved nod to his significant contributions to the success of the duo. I had no knowledge of I'm Glad There Is You (In a World of Trouble), but one listen to Natalie Cole doing the song, and I instantly got it. Gemini did include one song outside the timeframe- a note to not paying exact attention to what was asked for- however well it would fit on the collection.
My Conclusions on All Three Platforms: The knowledge base of each is very different. Not a single one was better than the offer, each just provided a unique response set. The knowledge base on Carpenters musical contribution seemed varied at best. As expected, not a single platform mentioned that Richard recorded a version of The Very Thought of You for a Japanese television special in the 90's. It seemed for all three that they took a deep look at Linda Ronstadt's great What's New album for inspiration in both song selection and style.
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Just for fun, I designed an imaginary concert that featured a Standards segment as its centerpiece. You can read about it here.
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I thought I'd end with something real from Richard on the subject of his sister singing the standards.
Goldmine magazine interview with Ken Sharp, July 22, 2022
GM: Let’s close with a hypothetical question. If you could be with Karen again, even for an hour, and you were told you can you talk about things and you can play piano and she can sing a few songs with you, what would you talk about and what songs would you choose to have her to sing?
RC: Well, I would once again let her know just how damn great a singer she was. One of the songs I would do with her would be “But Beautiful.” It’s from one of the Bing Crosby road pictures and went on to be a standard.
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